Di-hydro-cyclam dimaleate [H2(cyclam)(maleate)2].

The asymmetric unit of the title mol-ecular salt [systematic name: 1,4,8,11-tetraazacyclotetradecane-1,8-diium bis(3-carboxy-prop-2-enoate)], C10H26N4 (2+)·2C4H3O4 (-), contains two half-cations (both completed by crystallographic inversion symmetry) and two maleate anions. The cyclam macrocycles adopt trans-III conformations, supported by two intra-molecular N-H⋯O hydrogen bonds. The O-bonded H atom of each maleate ion is disordered over two positions with an occupancy ratio of 0.61 (5):0.39 (5): each one generates an intra-molecular O-H⋯O hydrogen bond. In the crystal, the cations are linked to the anions by N-H⋯O hydrogen bonds, generating [001] chains.

Related literature

For related cyclam crystal structures, see: Robinson et al. (1989) ▶; Frémond et al. (2000 ▶); Meyer et al. (1998 ▶). For macrocycle conformations, see: Bosnich et al. (1965 ▶); Dale (1973 ▶, 1976 ▶); Melson (1979 ▶); Bandoli et al. (1993 ▶); Hancock et al. (1996 ▶).

Experimental

Crystal data

C10H26N4 2+·2C4H3O4 −

M = 432.48

Monoclinic,

a = 8.2925 (1) Å

b = 13.5841 (2) Å

c = 19.2995 (3) Å

β = 98.797 (1)°

V = 2148.44 (5) Å3

Z = 4

Cu Kα radiation

μ = 0.89 mm−1

T = 100 K

0.25 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.81, T max = 0.84

18854 measured reflections

4018 independent reflections

3821 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.083

S = 1.04

4018 reflections

403 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813025580/hb7135sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813025580/hb7135Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H26N42+·2C4H3O4−	Z = 4
Mr = 432.48	F(000) = 928
Monoclinic, P21/n	Dx = 1.337 Mg m−3
a = 8.2925 (1) Å	Cu Kα radiation, λ = 1.54178 Å
b = 13.5841 (2) Å	µ = 0.89 mm−1
c = 19.2995 (3) Å	T = 100 K
β = 98.797 (1)°	Prism, colourless
V = 2148.44 (5) Å3	0.25 × 0.20 × 0.20 mm

Bruker SMART CCD diffractometer	3821 reflections with I > 2σ(I)
ω scans	Rint = 0.024
Absorption correction: multi-scan (SADABS; Bruker, 2005)	θmax = 70.1°, θmin = 4.6°
Tmin = 0.81, Tmax = 0.84	h = −10→9
18854 measured reflections	k = −16→16
4018 independent reflections	l = −23→23

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0406P)2 + 0.6721P] where P = (Fo2 + 2Fc2)/3
4018 reflections	(Δ/σ)max < 0.001
403 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.29130 (13)	0.94686 (8)	0.28537 (6)	0.0241 (2)
C2	0.42219 (13)	0.89074 (8)	0.25661 (6)	0.0240 (2)
C3	0.44193 (13)	0.87391 (8)	0.19031 (6)	0.0229 (2)
C4	0.34069 (12)	0.90322 (8)	0.12233 (6)	0.0227 (2)
C5	0.98341 (14)	0.76765 (8)	0.18188 (6)	0.0260 (2)
C6	1.05748 (14)	0.70568 (9)	0.24264 (6)	0.0259 (2)
C7	1.02908 (14)	0.70577 (9)	0.30874 (6)	0.0274 (2)
C8	0.92026 (14)	0.76946 (9)	0.34489 (6)	0.0284 (2)
C9	0.25226 (15)	0.61005 (9)	0.03030 (6)	0.0301 (3)
C10	0.47726 (15)	0.63339 (9)	0.13169 (7)	0.0303 (3)
C11	0.62753 (15)	0.58461 (10)	0.17098 (6)	0.0319 (3)
C12	0.75542 (14)	0.55991 (10)	0.12458 (7)	0.0309 (3)
C13	0.81528 (14)	0.46284 (9)	0.02577 (6)	0.0289 (3)
C14	0.75571 (15)	−0.17204 (9)	−0.00831 (7)	0.0313 (3)
C15	0.74127 (14)	−0.02422 (9)	0.06666 (6)	0.0283 (2)
C16	0.84068 (14)	0.05815 (9)	0.10416 (6)	0.0281 (2)
C17	1.02932 (15)	0.19107 (9)	0.08931 (6)	0.0306 (3)
C18	1.12976 (16)	0.24033 (9)	0.03941 (7)	0.0335 (3)
N1	0.38474 (12)	0.56356 (7)	0.08060 (5)	0.0245 (2)
N2	0.69367 (11)	0.48659 (7)	0.07078 (5)	0.0258 (2)
N3	0.84805 (11)	−0.09675 (7)	0.03828 (5)	0.0243 (2)
N4	0.92438 (12)	0.11249 (7)	0.05474 (5)	0.0248 (2)
O1	0.18816 (10)	0.99727 (6)	0.24442 (4)	0.03003 (19)
H1O	0.2061	0.9906	0.203	0.045*	0.39 (5)
O2	0.29456 (10)	0.94215 (6)	0.35007 (4)	0.0326 (2)
O3	0.22552 (10)	0.96878 (6)	0.12282 (4)	0.02853 (19)
O4	0.37276 (9)	0.86677 (6)	0.06808 (4)	0.02820 (19)
O5	0.85713 (11)	0.82014 (7)	0.18682 (5)	0.0352 (2)
H5O	0.8402	0.8206	0.2286	0.053*	0.41 (5)
O6	1.04578 (11)	0.76384 (7)	0.12791 (4)	0.0332 (2)
O7	0.81387 (10)	0.82564 (7)	0.30773 (5)	0.0340 (2)
O8	0.93463 (12)	0.76651 (8)	0.40874 (5)	0.0430 (2)
H1A	0.3368 (19)	0.5175 (12)	0.1059 (8)	0.036 (4)*
H1B	0.4603 (19)	0.5331 (11)	0.0571 (8)	0.034 (4)*
H2	0.4994 (17)	0.8649 (10)	0.2919 (7)	0.026 (3)*
H2A	0.6715 (18)	0.4294 (12)	0.0937 (8)	0.035 (4)*
H3	0.5346 (17)	0.8353 (10)	0.1825 (7)	0.026 (3)*
H3A	0.9173 (18)	−0.0670 (11)	0.0134 (8)	0.032 (4)*
H3B	0.9109 (19)	−0.1278 (11)	0.0739 (8)	0.034 (4)*
H3O	0.211 (3)	0.9802 (17)	0.1673 (15)	0.023 (8)*	0.61 (5)
H4	0.8494 (19)	0.1373 (11)	0.0233 (8)	0.033 (4)*
H6	1.1379 (17)	0.6605 (11)	0.2304 (8)	0.031 (3)*
H7	1.0899 (18)	0.6622 (12)	0.3405 (8)	0.035 (4)*
H7O	0.829 (3)	0.826 (2)	0.2615 (19)	0.033 (10)*	0.59 (5)
H9A	0.3008 (18)	0.6660 (12)	0.0107 (8)	0.036 (4)*
H9B	0.1683 (17)	0.6323 (11)	0.0580 (8)	0.031 (3)*
H10A	0.5089 (18)	0.6906 (11)	0.1055 (8)	0.033 (4)*
H10B	0.4040 (17)	0.6548 (11)	0.1624 (8)	0.031 (3)*
H11A	0.6791 (19)	0.6312 (12)	0.2085 (8)	0.039 (4)*
H11B	0.5941 (17)	0.5260 (11)	0.1945 (8)	0.031 (3)*
H12A	0.7842 (17)	0.6192 (11)	0.0991 (7)	0.030 (3)*
H12B	0.855 (2)	0.5371 (11)	0.1536 (8)	0.038 (4)*
H13A	0.8453 (17)	0.5260 (11)	0.0028 (7)	0.028 (3)*
H13B	0.9123 (19)	0.4366 (11)	0.0525 (8)	0.033 (4)*
H14A	0.6835 (18)	−0.1343 (11)	−0.0437 (8)	0.034 (4)*
H14B	0.6853 (19)	−0.2065 (12)	0.0195 (8)	0.039 (4)*
H15A	0.6656 (17)	0.0007 (10)	0.0272 (7)	0.025 (3)*
H15B	0.6817 (18)	−0.0594 (11)	0.0973 (8)	0.034 (4)*
H16A	0.9219 (17)	0.0315 (10)	0.1411 (7)	0.028 (3)*
H16B	0.7675 (18)	0.1014 (11)	0.1274 (8)	0.033 (4)*
H17A	1.1036 (17)	0.1611 (10)	0.1290 (7)	0.028 (3)*
H17B	0.9618 (18)	0.2419 (12)	0.1109 (8)	0.036 (4)*
H18A	1.0582 (19)	0.2722 (11)	0.0018 (8)	0.036 (4)*
H18B	1.1958 (19)	0.2909 (12)	0.0640 (8)	0.039 (4)*

	U11	U22	U33	U12	U13	U23
C1	0.0230 (5)	0.0242 (5)	0.0252 (5)	−0.0015 (4)	0.0038 (4)	−0.0028 (4)
C2	0.0228 (5)	0.0247 (5)	0.0235 (5)	0.0025 (4)	0.0007 (4)	0.0005 (4)
C3	0.0196 (5)	0.0231 (5)	0.0261 (5)	0.0023 (4)	0.0034 (4)	0.0001 (4)
C4	0.0201 (5)	0.0239 (5)	0.0243 (5)	−0.0021 (4)	0.0040 (4)	0.0022 (4)
C5	0.0261 (5)	0.0270 (5)	0.0238 (5)	−0.0043 (4)	0.0005 (4)	0.0003 (4)
C6	0.0235 (5)	0.0275 (6)	0.0261 (6)	0.0040 (4)	0.0025 (4)	−0.0013 (4)
C7	0.0267 (6)	0.0300 (6)	0.0245 (5)	0.0073 (5)	0.0006 (4)	0.0031 (5)
C8	0.0265 (6)	0.0319 (6)	0.0270 (6)	0.0035 (5)	0.0046 (4)	−0.0003 (5)
C9	0.0322 (6)	0.0314 (6)	0.0286 (6)	0.0088 (5)	0.0108 (5)	0.0045 (5)
C10	0.0332 (6)	0.0265 (6)	0.0337 (6)	−0.0034 (5)	0.0133 (5)	−0.0063 (5)
C11	0.0350 (6)	0.0339 (6)	0.0273 (6)	−0.0077 (5)	0.0066 (5)	−0.0046 (5)
C12	0.0243 (6)	0.0366 (6)	0.0312 (6)	−0.0054 (5)	0.0029 (5)	−0.0024 (5)
C13	0.0234 (5)	0.0362 (6)	0.0283 (6)	0.0052 (5)	0.0072 (5)	0.0056 (5)
C14	0.0302 (6)	0.0323 (6)	0.0291 (6)	−0.0103 (5)	−0.0024 (5)	0.0020 (5)
C15	0.0209 (5)	0.0360 (6)	0.0283 (6)	0.0020 (5)	0.0051 (4)	0.0075 (5)
C16	0.0259 (6)	0.0359 (6)	0.0230 (5)	0.0077 (5)	0.0056 (4)	−0.0002 (5)
C17	0.0331 (6)	0.0273 (6)	0.0290 (6)	0.0034 (5)	−0.0030 (5)	−0.0068 (5)
C18	0.0398 (7)	0.0236 (6)	0.0328 (6)	−0.0046 (5)	−0.0083 (5)	−0.0007 (5)
N1	0.0243 (5)	0.0245 (5)	0.0265 (5)	0.0006 (4)	0.0098 (4)	−0.0007 (4)
N2	0.0234 (5)	0.0284 (5)	0.0268 (5)	−0.0021 (4)	0.0082 (4)	0.0003 (4)
N3	0.0224 (5)	0.0269 (5)	0.0229 (5)	−0.0033 (4)	0.0007 (4)	0.0039 (4)
N4	0.0246 (5)	0.0258 (5)	0.0227 (5)	0.0031 (4)	−0.0009 (4)	−0.0007 (4)
O1	0.0262 (4)	0.0355 (4)	0.0282 (4)	0.0088 (3)	0.0038 (3)	−0.0013 (4)
O2	0.0365 (5)	0.0374 (5)	0.0247 (4)	0.0074 (4)	0.0076 (3)	−0.0025 (3)
O3	0.0278 (4)	0.0313 (4)	0.0257 (4)	0.0082 (3)	0.0017 (3)	0.0031 (3)
O4	0.0275 (4)	0.0357 (4)	0.0216 (4)	0.0025 (3)	0.0045 (3)	0.0008 (3)
O5	0.0337 (5)	0.0425 (5)	0.0286 (5)	0.0118 (4)	0.0026 (3)	0.0092 (4)
O6	0.0375 (5)	0.0395 (5)	0.0232 (4)	−0.0024 (4)	0.0064 (3)	0.0016 (3)
O7	0.0311 (4)	0.0404 (5)	0.0306 (5)	0.0142 (4)	0.0053 (3)	0.0018 (4)
O8	0.0473 (5)	0.0572 (6)	0.0254 (4)	0.0175 (5)	0.0083 (4)	−0.0004 (4)

C1—O2	1.2463 (14)	C13—N2	1.4641 (14)
C1—O1	1.2722 (14)	C13—C9i	1.5099 (18)
C1—C2	1.5007 (15)	C13—H13A	1.014 (15)
C2—C3	1.3343 (16)	C13—H13B	0.956 (16)
C2—H2	0.930 (14)	C14—N3	1.4933 (15)
C3—C4	1.4991 (15)	C14—C18ii	1.5156 (19)
C3—H3	0.961 (14)	C14—H14A	0.981 (16)
C4—O4	1.2236 (14)	C14—H14B	0.972 (16)
C4—O3	1.3070 (14)	C15—N3	1.4843 (15)
C5—O6	1.2328 (14)	C15—C16	1.5076 (17)
C5—O5	1.2824 (15)	C15—H15A	0.971 (14)
C5—C6	1.4969 (16)	C15—H15B	0.954 (16)
C6—C7	1.3321 (17)	C16—N4	1.4625 (15)
C6—H6	0.962 (15)	C16—H16A	0.973 (14)
C7—C8	1.4975 (16)	C16—H16B	0.998 (15)
C7—H7	0.941 (16)	C17—N4	1.4712 (15)
C8—O8	1.2204 (15)	C17—C18	1.5213 (19)
C8—O7	1.2967 (15)	C17—H17A	0.994 (14)
C9—N1	1.4906 (15)	C17—H17B	1.017 (16)
C9—C13i	1.5099 (18)	C18—C14ii	1.5155 (19)
C9—H9A	0.963 (16)	C18—H18A	0.967 (16)
C9—H9B	0.988 (15)	C18—H18B	0.958 (17)
C10—N1	1.4929 (15)	N1—H1A	0.920 (17)
C10—C11	1.5093 (18)	N1—H1B	0.925 (16)
C10—H10A	0.984 (16)	N2—H2A	0.926 (16)
C10—H10B	0.956 (15)	N3—H3A	0.899 (16)
C11—C12	1.5262 (17)	N3—H3B	0.901 (16)
C11—H11A	1.007 (16)	N4—H4	0.868 (16)
C11—H11B	0.978 (15)	O1—H1O	0.84
C12—N2	1.4729 (16)	O3—H3O	0.90 (3)
C12—H12A	0.992 (15)	O5—H5O	0.84
C12—H12B	0.977 (16)	O7—H7O	0.92 (4)
O2—C1—O1	124.03 (10)	H13A—C13—H13B	108.0 (12)
O2—C1—C2	116.00 (10)	N3—C14—C18ii	111.28 (10)
O1—C1—C2	119.95 (10)	N3—C14—H14A	105.3 (9)
C3—C2—C1	130.06 (10)	C18ii—C14—H14A	113.4 (9)
C3—C2—H2	117.8 (8)	N3—C14—H14B	107.1 (9)
C1—C2—H2	112.1 (8)	C18ii—C14—H14B	112.9 (9)
C2—C3—C4	131.25 (10)	H14A—C14—H14B	106.4 (12)
C2—C3—H3	117.6 (8)	N3—C15—C16	110.89 (9)
C4—C3—H3	111.2 (8)	N3—C15—H15A	107.0 (8)
O4—C4—O3	122.45 (10)	C16—C15—H15A	111.0 (8)
O4—C4—C3	118.39 (10)	N3—C15—H15B	106.9 (9)
O3—C4—C3	119.12 (9)	C16—C15—H15B	111.8 (9)
O6—C5—O5	122.62 (11)	H15A—C15—H15B	109.1 (12)
O6—C5—C6	117.60 (10)	N4—C16—C15	109.92 (9)
O5—C5—C6	119.75 (10)	N4—C16—H16A	108.8 (8)
C7—C6—C5	129.66 (11)	C15—C16—H16A	110.0 (8)
C7—C6—H6	117.9 (9)	N4—C16—H16B	112.1 (8)
C5—C6—H6	112.5 (9)	C15—C16—H16B	109.1 (8)
C6—C7—C8	130.85 (11)	H16A—C16—H16B	106.9 (12)
C6—C7—H7	117.9 (9)	N4—C17—C18	112.03 (10)
C8—C7—H7	111.1 (9)	N4—C17—H17A	107.8 (8)
O8—C8—O7	122.06 (11)	C18—C17—H17A	109.5 (8)
O8—C8—C7	118.61 (11)	N4—C17—H17B	110.8 (8)
O7—C8—C7	119.33 (10)	C18—C17—H17B	110.4 (9)
N1—C9—C13i	110.16 (9)	H17A—C17—H17B	106.1 (12)
N1—C9—H9A	106.2 (9)	C14ii—C18—C17	114.74 (10)
C13i—C9—H9A	111.6 (9)	C14ii—C18—H18A	109.1 (9)
N1—C9—H9B	106.7 (8)	C17—C18—H18A	109.9 (9)
C13i—C9—H9B	111.9 (8)	C14ii—C18—H18B	106.9 (9)
H9A—C9—H9B	110.0 (12)	C17—C18—H18B	109.1 (9)
N1—C10—C11	110.75 (10)	H18A—C18—H18B	106.8 (13)
N1—C10—H10A	108.3 (9)	C9—N1—C10	114.46 (9)
C11—C10—H10A	109.9 (9)	C9—N1—H1A	107.3 (10)
N1—C10—H10B	106.9 (9)	C10—N1—H1A	107.6 (10)
C11—C10—H10B	112.1 (9)	C9—N1—H1B	110.9 (9)
H10A—C10—H10B	108.7 (12)	C10—N1—H1B	106.8 (9)
C10—C11—C12	113.34 (10)	H1A—N1—H1B	109.6 (13)
C10—C11—H11A	108.2 (9)	C13—N2—C12	111.75 (9)
C12—C11—H11A	107.7 (9)	C13—N2—H2A	107.7 (9)
C10—C11—H11B	108.7 (8)	C12—N2—H2A	107.7 (9)
C12—C11—H11B	111.5 (8)	C15—N3—C14	113.39 (9)
H11A—C11—H11B	107.3 (12)	C15—N3—H3A	111.3 (9)
N2—C12—C11	111.37 (10)	C14—N3—H3A	107.3 (9)
N2—C12—H12A	106.5 (8)	C15—N3—H3B	109.7 (10)
C11—C12—H12A	110.7 (8)	C14—N3—H3B	108.8 (10)
N2—C12—H12B	111.2 (9)	H3A—N3—H3B	106.0 (13)
C11—C12—H12B	109.8 (9)	C16—N4—C17	112.16 (9)
H12A—C12—H12B	107.1 (12)	C16—N4—H4	106.9 (10)
N2—C13—C9i	110.86 (10)	C17—N4—H4	110.3 (10)
N2—C13—H13A	108.1 (8)	C1—O1—H1O	109.5
C9i—C13—H13A	109.3 (8)	C4—O3—H3O	109.3 (14)
N2—C13—H13B	111.2 (9)	C5—O5—H5O	109.5
C9i—C13—H13B	109.4 (9)	C8—O7—H7O	111.2 (16)
O2—C1—C2—C3	172.92 (12)	C10—C11—C12—N2	−64.14 (14)
O1—C1—C2—C3	−8.76 (18)	N3—C15—C16—N4	63.16 (12)
C1—C2—C3—C4	−1.1 (2)	N4—C17—C18—C14ii	−60.25 (13)
C2—C3—C4—O4	−169.79 (12)	C13i—C9—N1—C10	171.04 (9)
C2—C3—C4—O3	12.43 (18)	C11—C10—N1—C9	−169.21 (10)
O6—C5—C6—C7	169.97 (12)	C9i—C13—N2—C12	−178.28 (10)
O5—C5—C6—C7	−11.73 (19)	C11—C12—N2—C13	179.69 (10)
C5—C6—C7—C8	−2.7 (2)	C16—C15—N3—C14	−171.53 (10)
C6—C7—C8—O8	−167.94 (13)	C18ii—C14—N3—C15	176.49 (10)
C6—C7—C8—O7	12.2 (2)	C15—C16—N4—C17	−177.39 (9)
N1—C10—C11—C12	67.08 (13)	C18—C17—N4—C16	173.98 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2iii	0.920 (17)	1.800 (17)	2.7074 (13)	168.1 (14)
N1—H1B···N2	0.925 (16)	2.015 (15)	2.8000 (13)	141.7 (13)
N2—H2A···O7iv	0.926 (16)	2.356 (16)	3.2134 (13)	153.9 (13)
N2—H2A···O8iv	0.926 (16)	2.379 (16)	3.2178 (14)	150.6 (13)
N3—H3A···N4ii	0.899 (16)	2.089 (16)	2.8046 (14)	135.8 (13)
N3—H3B···O5v	0.901 (16)	2.397 (16)	3.0713 (13)	131.7 (12)
N3—H3B···O6v	0.901 (16)	2.037 (16)	2.8982 (13)	159.5 (14)
N4—H4···O4i	0.868 (16)	2.348 (16)	3.1596 (12)	155.8 (13)
O3—H3O···O1	0.90 (3)	1.55 (3)	2.4444 (12)	178 (2)
O7—H7O···O5	0.92 (4)	1.50 (4)	2.4157 (13)	176 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.920 (17)	1.800 (17)	2.7074 (13)	168.1 (14)
N1—H1B⋯N2	0.925 (16)	2.015 (15)	2.8000 (13)	141.7 (13)
N2—H2A⋯O7ii	0.926 (16)	2.356 (16)	3.2134 (13)	153.9 (13)
N2—H2A⋯O8ii	0.926 (16)	2.379 (16)	3.2178 (14)	150.6 (13)
N3—H3A⋯N4iii	0.899 (16)	2.089 (16)	2.8046 (14)	135.8 (13)
N3—H3B⋯O5iv	0.901 (16)	2.397 (16)	3.0713 (13)	131.7 (12)
N3—H3B⋯O6iv	0.901 (16)	2.037 (16)	2.8982 (13)	159.5 (14)
N4—H4⋯O4v	0.868 (16)	2.348 (16)	3.1596 (12)	155.8 (13)
O3—H3O⋯O1	0.90 (3)	1.55 (3)	2.4444 (12)	178 (2)
O7—H7O⋯O5	0.92 (4)	1.50 (4)	2.4157 (13)	176 (3)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .